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Methyl 3,6-Di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside (CAS 68601-74-1)

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Alternate Names:
Man1-α-6[Man1-α-3]Man-α-OMe; Methyl O-α-D-Mannopyranosyl-(1→3)-O- [α-D-mannopyranosyl-(1→6)]-α-D-mannopyranoside; Methyl 3,6-Di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside
Application:
CAS Number:
68601-74-1
Molecular Weight:
518.48
Molecular Formula:
C19H34O16
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside is a glycoside compound frequently utilized in glycobiology research to investigate carbohydrate-protein interactions and enzymatic activities. The chemical structure consists of two α-D-mannopyranosyl residues linked by a glycosidic bond, with one of the mannose residues methylated at the 3 and 6 positions. Its mechanism of action primarily involves its role as a substrate or ligand in various enzymatic assays and binding studies. Researchers employ this compound to study the specificity, kinetics, and mechanism of glycoside hydrolases, glycosyltransferases, lectins, and carbohydrate-binding proteins. Additionally, it serves as a probe for analyzing glycan recognition and processing by glycosidases and glycosyltransferases in cellular and microbial systems. Moreover, Methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside facilitates the synthesis and characterization of complex carbohydrates and glycoconjugates, contributing to the advancement of synthetic glycobiology and the development of vaccines and biomaterials. Its versatility and utility make it a valuable tool in elucidating the roles of carbohydrates in various biological processes, including cell-cell recognition, host-pathogen interactions, and immune responses, thus expanding our understanding of glycobiology and its implications in health and disease.


Methyl 3,6-Di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside (CAS 68601-74-1) References

  1. Thermodynamic binding studies of lectins from the diocleinae subtribe to deoxy analogs of the core trimannoside of asparagine-linked oligosaccharides.  |  Dam, TK., et al. 2000. J Biol Chem. 275: 16119-26. PMID: 10747944
  2. Binding of multivalent carbohydrates to concanavalin A and Dioclea grandiflora lectin. Thermodynamic analysis of the 'multivalency effect'.  |  Dam, TK., et al. 2000. J Biol Chem. 275: 14223-30. PMID: 10799500
  3. Structural characterization of a mannose-binding protein-trimannoside complex using residual dipolar couplings.  |  Jain, NU., et al. 2003. J Mol Biol. 328: 451-62. PMID: 12691753
  4. Synthesis and affinities of C3-symmetric thioglycoside-containing trimannosides.  |  Bi, J., et al. 2015. Carbohydr Res. 412: 56-65. PMID: 26047464
  5. Syntheses of model oligosaccharides of biological significance. Synthesis of methyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-d-mannopyranoside and the corresponding mannobiosides.  |  Winnik, FM., et al. 1982. Carbohydr Res. 103: 15-28. PMID: 7105064
  6. A structure of the complex between concanavalin A and methyl-3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside reveals two binding modes.  |  Loris, R., et al. 1996. J Biol Chem. 271: 30614-8. PMID: 8940035
  7. Spectroscopic studies on the interaction of pradimicin BMY-28864 with mannose derivatives.  |  Fujikawa, K., et al. 1998. Glycobiology. 8: 407-14. PMID: 9499388
  8. Synthesis of a tri- and tetradeoxy analogue of methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside for investigation of the binding site of various plant lectins.  |  Oscarson, S. and Svahnberg, P. 1998. Carbohydr Res. 309: 207-12. PMID: 9741077
  9. Thermodynamics of binding of the core trimannoside of asparagine-linked carbohydrates and deoxy analogs to Dioclea grandiflora lectin.  |  Dam, TK., et al. 1998. J Biol Chem. 273: 32812-7. PMID: 9830027

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Methyl 3,6-Di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside, 10 mg

sc-221914
10 mg
$430.00